


Decisions and Chances

by thepeoplessong



Category: Critical Role (Web Series)
Genre: I have no idea how many chapters this will be, M/M, Random breakfast shinanagens, Shadowgast, they be TENSE!!!, they be angsty!!, they be confessing!!, what's sexier than wizards NOTHING
Language: English
Status: In-Progress
Published: 2021-02-11
Updated: 2021-02-16
Packaged: 2021-03-18 07:01:14
Rating: Not Rated
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,242
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/29364414
Author URL: https://archiveofourown.org/users/thepeoplessong/pseuds/thepeoplessong
Summary: *Canon divergent POST episode 124 but also still works after 125!*Chapter 1: The Nein have headed to bed for the night, but Caleb cannot sleep knowing the battle ahead. He knows Essek is two floors below him, and needs to speak to him for a moment alone, even if only to get to know him a little more.Things are TENSE. Things are DIFFICULT. Things are ANGSTY. The bois SPEAK ALONE FINALLY.
Relationships: Essek Thelyss/Caleb Widogast
Comments: 5
Kudos: 125





	1. Conversational Embers

**Author's Note:**

> HELLO this is my first fic since 2013, Critical Role has truly taken over my entire life lol. I haven't written fiction in SO SO long and would love to see your comments if you have them!
> 
> This fic is canon divergent after episode 124. It is what I like to imagine will happen once the Nein come back to Eiselcross to meet up with Essek/battle the Tomb Takers in a week or so. It involves Essek staying in the tower, and knowing about Caleb's past, and starts once the Nein have all gone to bed. Chapter two is the next morning, a brief conversation. 
> 
> Lots of love! I may continue this fic, we shall see!

Caleb tossed and turned and counted the hours as they passed through the night. He cast his mind back to late nights with Astrid and Eadwulf, dreaming up situations and facets of knowledge and immediately scurrying to the library to find the information they sought, regardless of the time of night, the library feeling like the most exciting adventure. Nowadays, the more people he met, the more he felt there was so much he didn’t know.

This is what bothered him most about Essek. The drow was a man with so much knowledge and power, such a complex mind, and no matter how Caleb tried to study the man, Essek never let Caleb know him deeply enough to satiate his yearning in the way a book ever could. 

He sat up in bed with a frustrated sigh, holding his head in his hands and pushing his hair back. If a clash with the Tomb Takers was on the horizon, everything could change with the drop of a hat. When would they get time to themselves after this? Would he and his friends even still be alive? There were too many possible outcomes where he did not get to see the Nein again. Where he did not get to see Essek again.

He breathed another heavy sigh, swung his legs over the side of the bed, pulled on his clothes, and made for the door. 

He stopped, his hand on the doorknob. 

“Frumpkin. I need you to go to the guest room and see if our drow friend is awake.” 

The cat gave an acknowledging _mrrrow_ , and set off for the fifth floor. Caleb knew he could snap his senses into Frumpkin, but somehow, having his cat peer in on Essek and then report back to him felt slightly less intrusive than seeing it for himself. He waited, hand still on the door, unsure what outcome he hoped for.

A minute passed, and the cat padded back into his room through a tunnel to Caleb’s left. A look and a purr from Frumpkin, and Caleb knew Essek was awake. The redhead composed himself, turned the handle, and made his way to the guest room downstairs. 

Unsure if the others were awake, he stayed as quiet as possible, barely whispering the command to open the central iris of the tower.

He floated down to the 5th floor, took a breath outside the only room without a moniker on the door, and gathered his nerves.

He knocked. 

_Silence._

Just when he thought Essek must have fallen asleep, with a slight anxious flutter of hope and guilt, he heard it.

“Caleb?” Essek’s tentative voice came from behind the closed door.

“ _Ja_. How did you know?”

“I didn’t.”

A beat passed and Caleb supressed all theories of why Essek had assumed or perhaps _hoped_ it was Caleb at his bedroom door in the middle of the night.

“May I come in?” he asked.

“It’s your creation.” came the drow’s voice, without missing a beat.

“It is your room.” 

_Silence._

Caleb moved to enter, but the doorknob turned while his hand was an inch away, and the door swung open to reveal Essek sitting in the room’s dark brown armchair, hand outstretched towards the open door. Caleb took a few steps in, an awkward sense of intruding, despite the fact he had created the entire space in his own head.

Essek looked up at the man, expectantly. His usual calm aloofness was peppered with a different look behind the eyes, almost waiting for Caleb’s permission to let his guard down.

“Shadowhand, I am not here to force you to feel your shame. I am perfectly aware you do not need any assistance in that regard” Caleb started, speaking quietly and pointedly. “You have informed the Nein that you have never let anyone close enough to _know_ you, that you are always playing too many sides of a field to allow yourself teammates. And that when you trusted us, your entire game shifted.” 

Essek looked over into the embers in the fireplace and stayed silent. 

“I have thought deeply about your situation and your secrets ever since we discovered them. I truly believed my mind had covered every possible outcome of how you would be feeling after leaving our ship that night. And yet, something I never expected, not even for a moment, was an immediate need for redemption.”

Essek glanced up at Caleb in quiet disbelief. “And why not? What makes you believe you knew me well enough to be surprised by any of my actions?”

“I do not claim to know you, Shadowhand. But I know myself. I know that when I met this group, I was a wholly different person than I am now. I know that when I met them, my past was so overtly present that there was no way I could ever let them think they knew me, no way I could trust them or let them trust me. My past would catch up to me, they would learn, and they would leave. And the time it took to even allow them to like me- “, Caleb faltered on the words and caught his breath. “Ah, I am still learning to allow them. The reason I was so surprised by your feelings, was the immediacy of them. You flipped a switch. It has been but six weeks since we saw you on that ship, and you are willing to call us friends, to trust us, to ally yourself with us. This is the first time since I have met you, that you have taken an option different than I myself did, even when I considered our likenesses seemed even closer than ever.”

Caleb walked to the fireplace and let his eyes glaze over, staring into the embers that Essek was so intent on looking into. Flickers of past visions started to enter his mind, and he focused back on talking. “You have pleaded guilty to all your many crimes so recently, and you are currently sitting in an armchair I created, in a whole plane of existence dedicated to my very dearest friends. And I feel a jealousy, Shadowhand.” 

“A jealousy?” Essek snapped, making Caleb whip his head round to face the man. “You feel a jealousy toward my complete lack of alliance, the fact I have never felt the warmth of friendship until I had already dug my grave? That I have meddled in order to satisfy my own needs to the point of having nowhere to run to but this brutal, frozen outpost?”

“I feel jealousy that you have the Nein to _make_ you feel this remorse. You have friends to run to. I could not say the same for the man I once was.”

Essek’s discomfort filled the room, and the silence was palpable. Caleb hated this feeling. He hated jealousy and the bitter taste it brought. And still, he provoked the silence once more, the bitter taste continuing as he spoke.

“Perhaps if I had had friends like Veth, and Beauregard, and Jester”, he almost spat out their names, as though the harder he said them, the more intense and apparent his love for them would be. “Perhaps if I had had them, and the rest of the Nein, to keep me in check when I was making my worst decisions, I would have had a very different life. You have that chance. And you have jumped at it within months. I regret…I regret not having that until it was too late for me.”

He found himself being absurdly honest with Essek, and could feel his ears turning red at the sheer defencelessness of it.

Essek rose. He wasn’t floating, and despite being a head shorter than Caleb, his presence was still imposing.

He didn’t speak. He simply walked to the fireplace and stood next to Caleb, his eyes on the embers as if searching for something. When he finally seemed to find it, his voice was calm and slow.

“Time, Caleb Widogast”, Essek started. “I have already lived for more time than you ever will, and yet you seem to have experienced more lifetimes’ worth of friendship, healing, and love than I ever could imagine. The Mighty Nein have achieved more in their short time together than I have alone in this long, long life.”

The drow seemed to have deflated slightly, as if the simple act of holding back verbal affection had been keeping him standing so tall, as if uttering the words had lessened his grandeur. He finally looked up at Caleb, his whole body turning to face the redhead, who kept his eyes on the fireplace.

“You have loved, Caleb. You have loved and felt and experienced and lost so deeply, so greatly.”

Despite not looking directly at the man, Caleb could feel the severity of Essek’s eyes burning into his shoulder. The difference between his total inability to look at Caleb only a week ago, and this unfaltering intensity, was unnerving. The jealousy still raged within him, mixed with a knot in his stomach that was desperate to let his guard down.

“What are you sayi-” Caleb started.

“I am saying that the life I have lived has been full of mistakes and bad decisions, almost all of which I regret now.” Essek cut him off. The harshness of his words made Caleb whip his head up to meet eyes with him.

“I am 120 years old, and I have never experienced a connection as natural as when I met your group. And while our differences and disparities are truly showing their faces tonight, I know you know how that connection feels.” Essek’s words bordered on urgent.

“I do.” Caleb said, slightly breathlessly, taken aback.

“I am not good. I am not faithful or loyal.” Essek continued. “I am not any of the things you have discovered in this family. And yet, I am somehow standing in your tower, dedicated to the ones you love.” Each of his words sounded like they stung him to say, like they hurt coming from his lips. 

“You, Caleb Widogast, changed every facet of what I believe. You have been through so much hurt, and are able to feel such a pure and brazen love for your compatriots, that you created a temple to them. And I am here in it.”

Caleb finally fully turned his body to fully face the other man, almost raising his hands in protest. “Essek, I-“

“Caleb, I have made thousands of bad decisions, taken thousands of rotten, terrible chances, to the point where I have had nothing at all to lose, until I met you all. And while I do not wish to take any more chances that will lead me to losing the Nein, there is one I must take.”

Caleb looked directly at the drow, a second of silence puncturing their outpouring of regrets.

“Then take it.” 

Essek took the back of Caleb’s head in his hand, and kissed Caleb hard on the mouth. Months of carefully chosen words and meticulously planned-out touches weaved together into one urgent moment, and for a second, Caleb’s jealousy washed away and was overtaken with blank desire. They kissed, and kissed, and breathed hot, desperate breaths into each other’s skin, until they finally broke apart, panting from the sheer release of tension.

Caleb leaned back slightly, causing Essek to look up at him, inquisitively.

“I have to go.”, the redhead muttered, looking everywhere but Essek’s eyes.

“Wait, Caleb, did I do-“

“No. I just have to.”

Caleb had let his guard down and enjoyed it for just a second too long, and he could feel the panic rising. The guilt swirling in his stomach, the itch on his forearms, the anger and confusion and blank white noise building in his mind.

He placed a hurried and absent kiss on Essek’s forehead and swept out of the room.

“ _Auf”_ , he muttered, making his way into the centre of the tower, rising up, past the 7th floor where his empty bed and sleeping cat lay waiting for him. 

“ _Fort, doch nicht vergessen”_ , Caleb whispered, floating into the 8th floor of the tower.

He landed on hard flooring, working on autopilot while his mind and body betrayed him.

He turned and opened a door, making his way inside.

The door to the 6th room shut, and Caleb sat down inside, ready to spend the evening as he truly deserved to.


	2. Did you sleep well?

**Summary for the Chapter:**

> Chapter two!  
> Once again, canon divergent POST ep124 and ep125. It is set when the Nein eventually come back to Eiselcross to re-meet with Essek and possibly battle the Tomb Takers. They have all just spent the night in the Tower (see chapter 1 for how that went!) and this morning's breakfast is slightly strained. 
> 
> Essek is not used to so many people asking about his comfort, and his anxiety is peppered with bits of novelty and niceness.

**Notes for the Chapter:**

> A shorter chapter! It's breakfast time woooo. The bois are NERVOUS.

It was a long night for Caleb.

When the morning came and the Nein sleepily headed downstairs from their chambers, Yasha was surprised to see Essek sitting alone at the large dining room table, staring into space.

“Morning, Essek. Did you, uh, did you sleep well?”

“I did, thank you Yasha. I have been admiring Caleb’s many cats... he has quite a mind in there.”

“Yes, they are very nice. You should try the yogurt covered bugs they make, they are super crunchy.” 

Before Essek could process this phrase, Jester came frolicking in.

“Essek you HAVE to watch this, have you seen the cats yet? Wait, ready for this okay okay so.” Jester cleared her throat and posed with one arm outstretched, and one hand cupped round her mouth as if blowing a trumpet. 

“MITTENS! I HAVE A GRAND REQUEST!” she announced.

A small dark grey cat came padding up to her with much less enthusiasm than she had clearly been hoping for. 

“Pretty pretty please will you go to the kitchen and make some _lovely_ breakfast for our _wonderful_ guest? Essek, what would you like for breakfast?”

“Ah, I um...surprise me, Jester.” he replied with a smile, part of him knowing he may regret this gamble. 

“SURPRISE HIM, MITTENS!” Jester continued in a booming voice, “but please also bring lots of pancakes and maybe some of those nice fluffy eggs from last time and also Yasha’s bugs and also toast and orange juice please thank you.”

Mittens trotted off to the kitchen, and Jester dramatically flopped down next to Yasha, very proud of her show.

“Did you sleep well, Essek?” she chirped.

“Yes, it was very comfortable Jester, thank you.”

Before the conversation could continue, Beau and Fjord stumbled in, already playfully at each other’s throats like two eight-year-old siblings, with Caduceus and Veth appearing sleepily behind them with yawns and tired eyes.

“I’m just saying, it’s not like the actual tower is moving when you sleep, Fjord”, Beau was saying.

“But it _feels_ like it, that’s the entire point of the hammock, so that I feel like I’m back on a ship”

“Okay but you do get that it’s not actually- oh morning Essek. Did you sleep okay?”

“Yes, thank you Beauregard. It was very pleasant.” 

“Would it have been better in a hammock?” she smirked, elbowing Fjord in the ribs.

Essek gave a small chuckle in response, aware he was not totally part of the joke, but glad to be at least some part of his friends’ nonsense nonetheless. The Nein’s chatter eased the consistent knot in his stomach slightly, but it was gaining increasingly tighter with every minute that Caleb had not joined them. He considered asking about him, but knew better than to entertain Jester’s teasing while he was this anxious.

Luckily, Mittens the cat arrived to distract him slightly, carrying a towering plate of pancakes on her tail. Six other cats followed with every manner of breakfast food imaginable, hopping up onto the table with incredible grace, and setting all the plates down one by one, until a feast lay in front of the group. Essek had seen all sorts of magic in his time, but having multiple fey cats bring him breakfast - and to share it with friends - felt like the most unique novelty he’d known in a long while. He only wished Caleb were here to join. 

Caduceus appeared to have finally woken up a little with the sight of food, and interrupted the drow’s thinking. 

“Did you sleep well, Mister Essek?”

“Ah - yes. I did, Caduceus. Thank you.” Essek replied, unsure why the group were all so intent on his comfort. 

A silence followed while the group ate their breakfast, and Essek found himself feeling awkward. He looked around at his friends, who were completely invested in their meal, completely at ease, and he realised; _this_ was the comfortable silence he had been yearning for. 

Beau immediately broke the silence.

“Where the hell is Caleb? How is he still asleep? Was he up all night reading _again?”_

“I think I heard Frumpkin up in the middle of the night, but then again there’s 100 cats in this place so who knows” Caduceus replied with a smile.

“I might go and see if he’s awake” Jester said, moving to get up from the table, but her plan was stopped when she saw Caleb in the doorway, tired eyes and straggly hair. He plopped himself down at the end of the long table. 

“ _Guten morgen”_ he said quietly. 

The Nein knew Caleb well enough not to pry into his silence, but Veth kept a steady eye on him as he lazily prodded some toast with a butter knife. Her focus shifted to Essek for a second, and just as she thought; the drow was studying Caleb intently. She quickly decided to keep a close eye on them both for the day. 

They ate for a little longer, the silence peppered with snippets of conversation, and Essek kept a tab on Caleb out the corner of his eye. The redhead did not look up from his plate at all, and barely ate two bites. Essek accidentally caught eye contact with Veth for a second, and felt her concern. 

The drow spoke up tentatively.

“Caleb, did you sleep well?”

“Yes, Essek, I did, _danke_.” Caleb said, looking up properly for the first time. He looked up right on cue, knowing Essek would be aware of exactly how much sleep he had gotten.

The knot in Essek’s stomach tightened even further as the light shined on Caleb’s skin properly. The dark bags underneath the redhead’s eyes were heavy, and his pale skin looked sallow and tired. Essek did not need magic to know that Caleb had not slept a wink. 

Caleb scratched his left forearm and mentally repeated to himself: " _they do not know about the sixth room. You have been in your chambers all night. They do not know about the sixth room.”_

He could not yet think about Essek, about their conversation, about his jealousy, about how he had revealed so much to the drow, about _that kiss_.

And yet, when he had looked up to reply to Essek’s question, all he could see looking back was a pair of deeply concerned eyes, and those beautiful dark features he had been so close to the night before. 

He picked up the rest of his toast and swiftly left the table, quickly sweeping out of the room, and headed up to his chambers without a word. 

Jester and Veth looked at each other, unsure whether to follow. 

Jester’s unsaid question was answered quickly, as Veth put a hand on her hand.

“I think it’s best to let him come to us just now” the halfling said. 

Jester nodded in agreement, but then saw that Essek had already left the table, was floating swiftly out the door, and she realised that Caleb would not be alone for long.


End file.
